Best of Bootstrapping: Bootstrapped a Travel Business to $5M

Under30Experiences Co-founder Matt Wilson has built a fantastic business using content marketing to sell travel experiences to young adults. Very cool! Here is our conversation from 2018.

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where did you grow up and in what kind of background?

Matt Wilson: I grew up in upstate New York. I grew up in a little tiny town called Stormville, New York. It’s about 60 minutes outside of New York City. It’s not really that close to the city, but it wasn’t extremely rural. I just started being an enterprising young man whether it was by mowing lawns or picking golf balls out of the local ponds. Selling the golf balls on eBay was my first online business. That really ignited the passion for entrepreneurship. Baseball cards would probably be the other thing that I was really passionate about when I was younger.

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Bootstrapping an EdTech Venture to $6M, Ready to Scale with AI: Daniel Santos, CEO of Prepory (Part 5)

Sramana Mitra: So, you were acquiring families through SEO mainly.

Daniel Santos: Yes, primarily SEO.

Sramana Mitra: So, that was not limited to South Florida anymore?

How Entrepreneurs Learn Through Honest Feedback

I want to share with you some things we have learned in running the 1Mby1M program since 2008. Over 700 free mentoring roundtables. Over 300k entrepreneurs have participated.

It is extremely difficult to give negative feedback to entrepreneurs without triggering a defensive reaction. I was not good at this when we started.

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Video FAQs

The Ultimate 1Mby1M Decision Guide: Restructuring Playbooks for Profitability

1. Will 1Mby1M help me pivot from a “growth-at-all-costs” approach to a “profit-first” model, if necessary?

Bootstrapping an EdTech Venture to $6M, Ready to Scale with AI: Daniel Santos, CEO of Prepory (Part 4)

Sramana Mitra: So, you were acquiring families through SEO mainly.

Daniel Santos: Yes, primarily SEO.

Sramana Mitra: So, that was not limited to South Florida anymore?

Daniel Santos: Not at all. At that point, we started working with families internationally and across many U.S. states.

Sramana Mitra: Around 2018, how many families are we talking about?

Bootstrapping an EdTech Venture to $6M, Ready to Scale with AI: Daniel Santos, CEO of Prepory (Part 3)

Sramana Mitra: Online’s fine. I’m not necessarily thinking that you’re already on AI in 2016–17, because that’s definitely not the time when AI was as pervasive as it is today. So, let’s go back to 2016–17. Tell me more about how the business was progressing. How many schools were you catering to in 2016–17? How were you finding them? How were you doing the sales process?

The Ultimate 1Mby1M Decision Guide: Additional Critical Considerations

1. How does the program help if my business “gets stuck” or if my idea is failing — will I be guided to pivot and how actionable is that feedback?

Bootstrapping an EdTech Venture to $6M, Ready to Scale with AI: Daniel Santos, CEO of Prepory (Part 2)

Sramana Mitra: Okay. Let’s go back to this point where you have three high schools that you’re working with to validate your business model. How much were they willing to pay you?